Every September I make the same mistake. I panic-buy one pair of shoes and wear them into the ground by November. This year I did the homework first.

Below are the five shapes I keep coming back to, from a loafer you can walk in all day to a red shoe that does the talking for you. Each one comes with a few pictures that made me want it and a board of eight pairs I would actually buy.

The loafer has gone soft, and I mean that as a compliment. The best ones this season are unstructured, a little slouchy, and happy with a white sock or a sheer black one. If you only buy one pair of shoes this fall, make it this.

A tall boot is the easiest way to make a skirt feel like fall. I like them close to the calf with a low or kitten heel, and in brown before black. Slouchy works too, as long as it looks like you meant it.

I resisted the Mary Jane for years because it felt too sweet. Then I tried one in velvet with a straight trouser and changed my mind. Keep the strap thin and the toe soft, and add a print if you want some bite.

Suede is the texture I miss most all summer. In a warm brown it goes with denim, grey, black and every camel coat I own. This is where I would put the boot, the moccasin and the flat I plan to wear until it snows.

One red shoe changes the whole outfit. I mostly mean oxblood and bordeaux, the color of a good glass of wine, with one brighter pair for the brave. Wear it with navy, grey or all black and let it do the work.

If I had to start from zero, I would buy the loafer and the tall boot first, then let the red shoe be the treat.